Inducing Social Self-Sorting in Organic Cages to Tune the Shape of the Internal Cavity

Valentina Abet, Filip T. Szczypiński, Marc A. Little, Valentina Santolini, Christopher D. Jones, Robert Evans, Craig Wilson, Xiaofeng Wu, Michael F. Thorne, Michael J. Bennison, Peng Cui, Andrew I. Cooper, Kim E. Jelfs, Anna G. Slater*

*Corresponding author for this work

Research output: Preprint or Working paperWorking paper


Many interesting target guest molecules have low symmetry, yet most methods for synthesising hosts result in highly symmetrical capsules. Methods of generating lower-symmetry pores are thus required to maximise the binding affinity in host-guest complexes. Here, we use mixtures of tetraaldehyde building blocks to access low-symmetry imine cages. Whether a low-energy cage is isolated can be correctly predicted from the thermodynamic preference observed in computational models. The stability of the observed structures depends on the geometrical match of the aldehyde building blocks. One bent aldehyde stands out as unable to assemble into high-symmetry cages—and the same aldehyde generates low-symmetry socially self-sorted cages when combined with a linear aldehyde. We exploit this finding to synthesise a family of low-symmetry cages containing heteroatoms, illustrating that pores of varying geometries and surface chemistries may be reliably accessed through computational prediction and self-sorting.
Original languageEnglish
Number of pages14
Publication statusPublished - 26 May 2020

Bibliographical note

Funding: EP/R005931/1
Leverhulme Trust Research Project Grant
Royal Society-EPSRC Dorothy Hodgkin Fellowship
Royal Society University Research Fellowship


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